The broad objective of this research is to explore selected areas of synthetic organic chemistry with the goals of (a) developing new synthetic methods, and (b) synthesizing new classes of compounds or new compounds of known types which have unusual or interesting structures and which may have useful pharmacologic properties (anti-viral, anti-cancer, anti-fertility, gastrointestinal, etc.). More specifically in the current grant period we will focus attention on cyclohexadienone epoxides, polyepoxides, epoxyketones, highly substituted and strained polynuclear aromatic compounds, and cycloalkenes containing strained double bonds (i.e., trans double bonds in rings with 8 or fewer atoms), as well as other functionality. BIBLIOGRAPHIC REFERENCES: H. Hart and J. Reilly, "The Chlorination of Hexamethylbenzene and Octamethylnaphthalene with Sulfuryl Chloride-Silica Gel (SC/SG)," Tetrahedron Lett., 143 (1977). E. Dunkelblum and Hart, "Stereochemistry and Mechanism of the Photochemical Addition of Methanol to Cycloheptenones", J. Am. Chem. Soc., 99, 644 (1977).